Blackwood presented the hit UK version of Singled Out on mainstream television channel, Channel 5 and, in 1999, presented his own show called The Richard Blackwood Show. He was also a presenter on MTV television show, MTV Select with Donna Air.

In 2000, Blackwood scored a number three hit single on the UK Singles Chart with the song “Mama Who Da Man”, based on Mama Used to Say by his uncle Junior. The single sold 200,000+ copies and was written and produced by Lucas Secon (Pussycat Dolls, Jordin Sparks, Sugababes) and Mickey P. He later followed it up with two singles, “ Get with the Wicked” (No. 10) and “Someone There for Me” (No. 23) and released the album You’ll Love to Hate This (No. 10) in late 2000.

Blackwood had acting appearances in Holby City in 2003 and played the title character in the 2002 television series Ed Stone Is Dead. In March 2007, he acted in the Bollywood smash-hit film Don’t Stop Dreaming. In 2005, Blackwood appeared in Princes of Comedy DVD release.

Blackwood was a presenter for the London radio station Choice FM and did some cover work on Capital FM.

In 2010, he played Brightie in the Tennessee Williams play Cat on a Hot Tin Roof, alongside Adrian Lester and James Earl Jones at the Novello Theatre in London.

In March 2011, he played the role of Russell – the Store Manager, in Anuvahood, starring Adam Deacon.

Also in 2011, he played the role of Donkey in the West End production of Shrek the Musical. The show opened at the Theatre Royal Drury Lane on 14 June 2011. He has starred alongside such performers as Amanda Holden, Nigel Lindsay, Nigel Harman, Kimberley Walsh and Neil McDermott.

Blackwood appeared with the rest of the Shrek cast on Britain’s Got Talent for ITV on 31 May 2011. They performed “I’m a Believer”.

On 17 January 2015, it was announced that Blackwood would be joining the cast of EastEnders as character Vincent Hubbard. He made his first appearance on 17 February 2015. His last appearance aired on 20 April 2018. He had previously been interviewed in a 2003 EastEnders documentary on the return of Den Watts.

In 2019, Blackwood took part in the eleventh series of Dancing on Ice, partnered with a newcomer Carlotta Edwards. They was eliminated in Week 3 following a skate off between Loose Women’s Saira Khan and her partner Mark Hanretty who was saved by overriding vote.